For a humorous magazine, Spy often was aggressive about straight feature reporting. In the summer of 1992, it ran the only serious investigative story on President George H.W. Bush's extramarital affairs with Jennifer Fitzgerald and other women.[4] The following year, Spy ran an article entitled "Clinton's First 100 Lies", detailing what it described as the new president's pattern of duplicitous behavior.[5]

Introduced in the May 1987 issue, Private Lives of Public Enemies (renamed Private Lives of Public Figures, then simply Private Lives in 1989) presented fictional representations of public personalities in unflattering situations.

Separated at Birth, first presented in a feature article in December 1987, would juxtapose two photos, usually one of a public personality with that of another public personality, popular character, etc. The comparison, and sometimes the photos themselves, were comical.

In October 2006, Miramax Books published Spy: The Funny Years (ISBN 1-4013-5239-1), a greatest-hits anthology and history of the magazine created and compiled by Carter, Andersen, and one of their original editors, George Kalogerakis.